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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:34 UTC
HMDB IDHMDB0014394
Secondary Accession Numbers
  • HMDB14394
Metabolite Identification
Common NameIdoxuridine
DescriptionIdoxuridine is only found in individuals that have used or taken this drug. It is an analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent. [PubChem]Idoxuridine acts as an antiviral agent by inhibiting viral replication by substituting itself for thymidine in viral DNA. This in turn inhibits thymidylate phosphorylase and viral DNA polymerases from properly functioning. The effect of Idoxuridine results in the inability of the virus to reproduce or to infect/destroy tissue.
Structure
Data?1582753174
Synonyms
ValueSource
(+)-5-Iodo-2'-deoxyuridineChEBI
1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracilChEBI
1-beta-D-2'-Deoxyribofuranosyl-5-iodouracilChEBI
1beta-D-2'-Deoxyribofuranosyl-5-iodouracilChEBI
2'-Deoxy-5-iodouridineChEBI
5-IododeoxyuridineChEBI
5-Iodouracil deoxyribosideChEBI
IdoxuridinChEBI
IdoxuridinaChEBI
IdoxuridinumChEBI
IdUChEBI
IododeoxyridineChEBI
IodoxuridineChEBI
JoddeoxiuridinChEBI
DendridKegg
HerplexKegg
1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracilGenerator
1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracilGenerator
1-b-D-2'-Deoxyribofuranosyl-5-iodouracilGenerator
1-Β-D-2'-deoxyribofuranosyl-5-iodouracilGenerator
1b-D-2'-Deoxyribofuranosyl-5-iodouracilGenerator
1Β-D-2'-deoxyribofuranosyl-5-iodouracilGenerator
5IDUHMDB
5IUDRHMDB
Allergan 201HMDB
Allergan 211HMDB
ID2HMDB
IdossuridinaHMDB
IDURHMDB
IUDRHMDB
3H-Labeled idoxuridineHMDB
KerecideHMDB
Liquifilm, herplexHMDB
StoxilHMDB
5 Iodo 2' deoxyuridineHMDB
5-Iodo-2'-deoxyuridineHMDB
Idoxuridine, 123I-labeledHMDB
Idoxuridine, 131I-labeledHMDB
Idoxuridine, 3H labeledHMDB
Herplex liquifilmHMDB
Idoxuridine, 125I-labeledHMDB
Idoxuridine, 3H-labeledHMDB
Idoxuridine, radical ion (+1)HMDB
Idoxuridine, radical ion (1-)HMDB
IododeoxyuridineHMDB
Oftan-iduHMDB
SK And F-14287HMDB
123I-labeled idoxuridineHMDB
125I-labeled idoxuridineHMDB
131I-labeled idoxuridineHMDB
5 IododeoxyuridineHMDB
Idoxuridine, 123I labeledHMDB
Idoxuridine, 125I labeledHMDB
Idoxuridine, 131I labeledHMDB
Oftan iduHMDB
OftanIDUHMDB
IdoxuridineChEBI
Chemical FormulaC9H11IN2O5
Average Molecular Weight354.0985
Monoisotopic Molecular Weight353.971264892
IUPAC Name1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nameidoxuridine
CAS Registry Number54-42-2
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O
InChI Identifier
InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChI KeyXQFRJNBWHJMXHO-RRKCRQDMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Halopyrimidine
  • Hydroxypyrimidine
  • Pyrimidone
  • Aryl halide
  • Aryl iodide
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 166 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility23.4 g/LNot Available
LogP-0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility23.4 g/LALOGPS
logP-0.7ALOGPS
logP-0.53ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.4 m³·mol⁻¹ChemAxon
Polarizability26.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9044000000-bccd33421cbd5827f9e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0v6u-9642400000-d09550b7622d0c69b6ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-503ffdc301f622376ef7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-e66a7d844dfee68481bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0690000000-4c754856d776ee07cebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ktf-5079000000-7500193a38a21df71a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-1193000000-e1259b68275318de6919Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-be831d327a49e1e8662cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00249 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00249 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00249
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIdoxuridine
METLIN IDNot Available
PubChem Compound5905
PDB IDID2
ChEBI ID147675
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fauth E, Zankl H: Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. Mutat Res. 1999 Apr 6;440(2):147-56. [PubMed:10209337 ]
  2. Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. [PubMed:10392098 ]
  3. Seth AK, Misra A, Umrigar D: Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. Pharm Dev Technol. 2004 Aug;9(3):277-89. [PubMed:15458233 ]